1458
N. Mori, H. Togo
LETTER
(4) (a) Furukawa, N.; Fukumura, M.; Akasaka, T.; Yoshimura,
T.; Oae, S. Tetrahedron Lett. 1980, 21, 761. (b) Yamazaki,
S.; Yamazaki, Y. Chem. Lett. 1990, 571. (c) Bose, D. S.;
Narsaiah, A. V. Tetrahedron Lett. 1998, 39, 6533.
(d) Chen, F.-E.; Fu, H.; Meng, G.; Cheng, Y.; Lü, Y.-X.
Synthesis 2000, 1519. (e) Erman, M. B.; Snow, J. W.;
Williams, M. J. Tetrahedron Lett. 2000, 41, 6749. (f) Lai,
G.; Bhamare, N. K.; Anderson, W. K. Synlett 2001, 230.
(g) Sharghi, H.; Sarvari, M. H. Tetrahedron 2002, 58, 10323.
(5) (a) Lehnert, W. Tetrahedron Lett. 1971, 1501.
(b) Campagna, F.; Carotti, A.; Casini, G. Tetrahedron Lett.
1977, 1813. (c) Heck, M.-P.; Wagner, A.; Mioskowski, C. J.
Org. Chem. 1996, 61, 6486. (d) Nakajima, N.; Ubukata, M.
Tetrahedron Lett. 1997, 38, 2099. (e) Bose, D. S.;
Jayalakshmi, B. J. Org. Chem. 1999, 64, 1713. (f) Bose, D.
S.; Narsaiah, A. V. Synthesis 2001, 373.
(6) (a) Kukhar, V. P.; Pasternak, V. I. Synthesis 1974, 563.
(b) Meshram, H. M. Synthesis 1992, 943. (c) Fukuzawa, S.-
I.; Yamaishi, Y.; Furuya, H.; Terao, K.; Iwasaki, F.
Tetrahedron Lett. 1997, 38, 7203. (d) Wang, E.-C.; Lin, G.-
J. Tetrahedron Lett. 1998, 39, 4047.
(7) (a) Misono, A.; Osa, T.; Koda, S. Bull. Chem. Soc. Jpn.
1966, 39, 854. (b) Misono, A.; Osa, T.; Koda, S. Bull. Chem.
Soc. Jpn. 1967, 40, 2875. (c) Talukdar, S.; Hsu, J.-L.; Chou,
T.-C.; Fang, J.-M. Tetrahedron Lett. 2001, 42, 1103.
(8) (a) Jereb, M.; Zupan, M.; Stavber, S. Chem. Commun. 2004,
2614. (b) Barluenga, J.; Marco-Arias, M.; González-Bobes,
F.; Ballesteros, A.; González, J. M. Chem. Commun. 2004,
2616.
References
(1) (a) Friedrick, K.; Wallensfels, K. The Chemistry of the
Cyano Group; Rappoport, Z., Ed.; Wiley-Interscience: New
York, 1970. (b) North, M. Comprehensive Organic
Functional Group Transformations; Katritzky, A. R.; Meth-
Cohn, O.; Rees, C. W., Eds.; Pergamon: Oxford, 1995.
(2) (a) Wipf, P. Chem. Rev. 1995, 95, 2115. (b) Wipf, P.;
Yokokawa, F. Tetrahedron Lett. 1998, 39, 2223.
(c) Ducept, P. C.; Marsden, S. P. Synlett 2000, 692.
(d) Chihiro, M.; Nagamoto, H.; Takemura, I.; Kitano, K.;
Komatsu, H.; Sekiguchi, K.; Tabusa, F.; Mori, T.;
Tominaga, M.; Yabuuchi, Y. J. Med. Chem. 1995, 38, 353.
(e) Gu, X.-H.; Wan, X.-Z.; Jiang, B. Bioorg. Med. Chem.
Lett. 1999, 9, 569. (f) Kadaba, P. K. Synthesis 1973, 71.
(g) Diana, G. D.; Cutcliffe, D.; Volkots, D. L.; Mallamo, J.
P.; Bailey, T. R.; Vescio, N.; Oglesby, R. C.; Nitz, T. J.;
Wetzel, J.; Giranda, V.; Pevear, D. C.; Dutko, F. J. J. Med.
Chem. 1993, 36, 3240. (h) Wittenberger, S. J.; Donner, B.
G. J. Org. Chem. 1993, 58, 4139. (i) Shie, J.-J.; Fang, J.-M.
J. Org. Chem. 2003, 68, 1158. (j) Medwid, J. B.; Paul, R.;
Baker, J. S.; Brockman, J. A.; Du, M. T.; Hallett, W. A.;
Hanifin, J. W.; Hardy, R. A. Jr.; Tarrant, M. E.; Torley, I.
W.; Wrenn, S. J. Med. Chem. 1990, 33, 1230. (k) Khanna,
I. K.; Weier, R. M.; Yu, Y.; Xu, X. D.; Koszyk, F. J.; Collins,
P. W.; Koboldt, C. M.; Veenhuizen, A. W.; Perkins, W. E.;
Casler, J. J.; Masferrer, J. L.; Zhang, Y. Y.; Gregory, S. A.;
Seibert, K.; Isakson, P. C. J. Med. Chem. 1997, 40, 1634.
(3) (a) Kametani, T.; Takahashi, K.; Ohsawa, T.; Ihara, M.
Synthesis 1977, 245. (b) Feldhues, U.; Schäfer, H. J.
Synthesis 1982, 145. (c) Capdevielle, P.; Lavigne, A.;
Maumy, M. Synthesis 1989, 453. (d) Yamazaki, S.;
Yamazaki, Y. Bull. Chem. Soc. Jpn. 1990, 63, 301.
(e) Capdevielle, P.; Lavigne, A.; Sparfel, D.; Baranne-
Lafont, J.; Cuong, N. K.; Maumy, M. Tetrahedron Lett.
1990, 31, 3305. (f) Gao, S.; Herzig, D.; Wang, B. Synthesis
2001, 544. (g) Chen, F.-E.; Kuang, Y.-Y.; Dai, H.-F.; Lu, L.;
Huo, M. Synthesis 2003, 2629. (h) Luca, L. D.; Giacomelli,
G. Synlett 2004, 2180.
(9) Barluenga, J.; González-Bobes, F.; Murguía, M. C.;
Ananthoju, S. R.; González, J. M. Chem.–Eur. J. 2004, 10,
4206.
(10) Miller, R. A.; Hoerrner, R. S. Org. Lett. 2003, 5, 285.
(11) Chen, F.-E.; Li, Y.-Y.; Xu, M.; Jia, H.-Q. Synthesis 2002,
1804.
(12) (a) Togo, H.; Katohgi, M. Synlett 2000, 565. (b) Togo, H.;
Harada, Y.; Yokoyama, M. J. Org. Chem. 2000, 65, 926.
(c) Katohgi, M.; Togo, H. Tetrahedron 2001, 57, 7481.
(d) Mori, N.; Togo, H. Synlett 2004, 880.
(13) CAUTION: It is known that iodine reacts with ammonia
water under certain conditions to give a black powder of
nitrogen triiodide monoamine (NI3·NH3). The dry powder
explodes readily by mechanical shock, heat or irradiation.
Although we did not have any incidents in this study, one
should be careful.
(14) Online data from Sigma-Aldrich products;
Synlett 2005, No. 9, 1456–1458 © Thieme Stuttgart · New York